Stop offering upgrades as if they were updates.
You software goes out and looks for a update every time it's started and then pops up a little notice. When I clicked on this thinking I was getting an update to my existing software, it installed a new trial version and uninstalled my older licensed version. This is not only irritating, I think it is underhanded and reprehensible.
The new update mechanism (the blue bar at the top of the screen) should make it much clearer when your support & upgrades status means you’re not entitled to a major version upgrade, and therefore upgrading would start a new trial instead.
If you have a v1 license with Support & Upgrades, then you will need to reactivate your license. You can do this in SSMS on the SQL Source Control tab by selecting Help > Enter Serial Number in the upper right corner. To look up your serial number, you can use https://www.red-gate.com/dynamic/endusers/enduserlogin.
I just upgraded SQL Source Control, restarted SSMS and now it shows that it is in trial mode and is only valid for 27 days! :-(